Literature DB >> 575041

Cell-free conversion of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine into an antibiotic with the properties of isopenicillin N in Cephalosporium acremonium.

T Konomi, S Herchen, J E Baldwin, M Yoshida, N A Hunt, A L Demain.   

Abstract

Cell-free extracts of antibiotic-negative mutants of Cephalosporium acremonium converted delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine (LLD-tripeptide) into an antibiotic that was destroyed by penicillinase. The enzymic activity of the extracts was destroyed by boiling, but was not inhibited by cycloheximide. LLL-Tripeptide was totally inactive as substrate. The product resembled isopenicillin N, but not penicillin N, in its antibacterial spectrum. We propose that isopenicillin N is the first product of cyclization of LLD-tripeptide.

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Year:  1979        PMID: 575041      PMCID: PMC1161778          DOI: 10.1042/bj1840427

Source DB:  PubMed          Journal:  Biochem J        ISSN: 0264-6021            Impact factor:   3.857


  9 in total

1.  Aminoadipylpenicillin in penicillin fermentations.

Authors:  M COLE; F R BATCHELOR
Journal:  Nature       Date:  1963       Impact factor: 49.962

2.  Conversion of penicillin N to cephalosporin(s) by cell-free extracts of Cephalosporium acremonium.

Authors:  M Kohsaka; A L Demain
Journal:  Biochem Biophys Res Commun       Date:  1976-05-17       Impact factor: 3.575

3.  Studies on the cell-free biosynthesis of beta-lactam antibiotics.

Authors:  P E Bost; A L Demain
Journal:  Biochem J       Date:  1977-03-15       Impact factor: 3.857

4.  Cell-free ring expansion of penicillin N to deacetoxycephalosporin C by Cephalosporium acremonium CW-19 and its mutants.

Authors:  M Yoshida; T Konomi; M Kohsaka; J E Baldwin; S Herchen; P Singh; N A Hunt; A L Demain
Journal:  Proc Natl Acad Sci U S A       Date:  1978-12       Impact factor: 11.205

5.  Formation and properties of protoplasts from antibiotic-producing strains of Penicillium chrysogenum and Cephalosporium acremonium.

Authors:  P A Fawcett; P B Loder; M J Duncan; T J Beesley; E P Abraham
Journal:  J Gen Microbiol       Date:  1973-12

6.  Synthesis of tritium-labelled isopenicillin N, penicillin N and 6-aminopenicillanic acid.

Authors:  J J Usher; B Loder; E P Abraham
Journal:  Biochem J       Date:  1975-12       Impact factor: 3.857

7.  Synthesis of delta-(alpha-aminoadipyl)cysteinylvaline and its role in penicillin biosynthesis.

Authors:  P A Fawcett; J J Usher; J A Huddleston; R C Bleaney; J J Nisbet; E P Abraham
Journal:  Biochem J       Date:  1976-09-01       Impact factor: 3.857

8.  Incorporation of 3H from delta-(L-alpha-amino (4,5-3H)adipyl)-L-cysteinyl-D-(4,4-3H)valine into isopenicillin N.

Authors:  J O'Sullivan; R C Bleaney; J A Huddleston; E P Abraham
Journal:  Biochem J       Date:  1979-11-15       Impact factor: 3.857

9.  Preparation of penicillin N and isopenicillin N.

Authors:  H Vanderhaeghe; A Vlietinck; M Claesen; G Parmentier
Journal:  J Antibiot (Tokyo)       Date:  1974-03       Impact factor: 2.649

  9 in total
  17 in total

Review 1.  Nonribosomal peptide synthetases involved in the production of medically relevant natural products.

Authors:  Elizabeth A Felnagle; Emily E Jackson; Yolande A Chan; Angela M Podevels; Andrew D Berti; Matthew D McMahon; Michael G Thomas
Journal:  Mol Pharm       Date:  2008-01-25       Impact factor: 4.939

2.  Cell-free conversion of isopenicillin N into deacetoxycephalosporin C by Cephalosporium acremonium mutant M-0198.

Authors:  J E Baldwin; J W Keeping; P D Singh; C A Vallejo
Journal:  Biochem J       Date:  1981-02-15       Impact factor: 3.857

Review 3.  Antibiotic resistance in pathogenic and producing bacteria, with special reference to beta-lactam antibiotics.

Authors:  H Ogawara
Journal:  Microbiol Rev       Date:  1981-12

Review 4.  Molecular regulation of beta-lactam biosynthesis in filamentous fungi.

Authors:  A A Brakhage
Journal:  Microbiol Mol Biol Rev       Date:  1998-09       Impact factor: 11.056

5.  Conversion of isopenicillin N into penicillin N in cell-free extracts of Cephalosporium acremonium.

Authors:  G S Jayatilake; J A Huddleston; E P Abraham
Journal:  Biochem J       Date:  1981-02-15       Impact factor: 3.857

6.  Stoichiometry of oxygen consumption in the biosynthesis of isopenicillin from a tripeptide.

Authors:  R L White; E M John; J E Baldwin; E P Abraham
Journal:  Biochem J       Date:  1982-06-01       Impact factor: 3.857

7.  Incorporation of 3H from delta-(L-alpha-amino (4,5-3H)adipyl)-L-cysteinyl-D-(4,4-3H)valine into isopenicillin N.

Authors:  J O'Sullivan; R C Bleaney; J A Huddleston; E P Abraham
Journal:  Biochem J       Date:  1979-11-15       Impact factor: 3.857

8.  Stereochemistry of the incorporation of valine methyl groups into methylene groups in cephalosporin C.

Authors:  C P Pang; R L White; E P Abraham; D H Crout; M Lutstorf; P J Morgan; A E Derome
Journal:  Biochem J       Date:  1984-09-15       Impact factor: 3.857

9.  Interference by methionine on valine uptake in Acremonium chrysogenum.

Authors:  M J Alonso; J M Luengo
Journal:  Antimicrob Agents Chemother       Date:  1987-02       Impact factor: 5.191

10.  A study of the biosynthesis of the tripeptide delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine in a beta-lactam-negative mutant of Cephalosporium acremonium.

Authors:  R M Adlington; J E Baldwin; M Lopez-Nieto; J A Murphy; N Patel
Journal:  Biochem J       Date:  1983-09-01       Impact factor: 3.857

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